4,5-dihydro-1H-1,2,4-triazole-3-carboxamide derivatives and herbicidal composition containing the same

Abstract

Disclosed herein is a 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide derivative represented by the formula (I): ##STR1## wherein R represents a straight-chain alkyl group having 1 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms or a branched alkyl group having 3 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms; X 1 represents a halogen atom or an alkyl group having 1 to 3 carbon atoms; X 2 represents hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Y 1 represents hydrogen atom or fluorine atom; and Y 2 represents hydrogen atom or fluorine atom. The derivatives of the formula (I) have high herbicidal activities and also show a excellent selectivity in their actions for killing weeds alone while doing any practical harm to the crops such as rice, wheat and corn.

What is claimed is: 
     
       1. A 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide derivative represented by the formula (I): ##STR26## wherein R represents a straight-chain alkyl group having 1 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms or a branched alkyl group having 3 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms; Xl represents a halogen atom or an alkyl group having 1 to 3 carbon atoms; X 2  represents hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Y 1  represents hydrogen atom or fluorine atom; and Y 2  represents hydrogen atom or fluorine atom. 
     
     
       2. The derivative according to claim 1, wherein said derivative is represented by the formula (I): ##STR27## wherein R represents a straight-chain alkyl group having 3 to 6 carbon atoms which is non-substituted or substituted with 3 to 12 fluorine atoms or a branched alkyl group having 3 to 6 carbon atoms which is non-substituted or substituted with 3 to 12 fluorine atoms; X 1  represents a halogen atom or an alkyl group having 1 to 3 carbon atoms; X 2  represents hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Y 1  represents hydrogen atom or fluorine atom; and Y 2  represents hydrogen atom or fluorine atom. 
     
     
       3. The derivative according to claim 2, wherein said derivative is represented by the formula (I): ##STR28## wherein R represents a straight-chain alkyl group having or 4 carbon atoms which is substituted with 5 to 7 fluorine atoms; X 1  represents a chlorine atom or a methyl group; and X 2 , Y 1  and Y 2  respectively represent hydrogen atom. 
     
     
       4. The derivative according to claim 3, wherein said derivative is 1-[4-chloro-3-[(2,2,3,3,3-pentafluoropropoxy)methyl]phenyl]-4,5-dihydro-5-phenyl-1H-1,2,4-triazole-3-carboxamide. 
     
     
       5. The derivative according to claim 3, wherein said derivative is 1-[4-methyl-3-[(2,2,3,3,3-pentafluoropropoxy)methyl]phenyl]-4,5-dihydro-5-phenyl-1H-1,2,4-triazole-3-carboxamide. 
     
     
       6. The derivative according to claim 3, wherein said derivative is 1-[4-chloro-3-[(2,2,3,3,4,4,4-heptafluorobutoxy)methyl]phenyl]-4,5-dihydro-5-phenyl-1H-1,2,4-triazole-3-carboxamide. 
     
     
       7. A herbicidal composition comprising as active ingredient a herbicidally effective amount of 4,5-dihydro-1H-1,2,4-triazole-3-carboxamide derivative represented by the formula (I): ##STR29## wherein R represents a straight-chain alkyl group having 1 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms or a branched alkyl group having to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms; X 1  represents a halogen atom or an alkyl group having 1 to 3 carbon atoms; X 2  represents hydrogen atom, a halogen atom or an alkyl group having 1 to 3 carbon atoms; Y 1  represents hydrogen atom or fluorine atom; and Y 2  represents hydrogen atom or fluorine atom, and herbicidally acceptable carrier and/or adjuvant.